Light-emitting element and light-emitting device

ABSTRACT

To provide a light-emitting element, a light-emitting device, and an electronic device each formed using the organometallic complex represented by General Formula (G1) as a guest material and a low molecule compound as a host material.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention disclosed hereinafter relates to a light-emittingelement using a phosphorescent compound. Further, the present inventionrelates to a light-emitting device using the light-emitting element andan electronic device using the light-emitting device.

2. Description of the Related Art

In recent years, a light-emitting element using a light-emitting organiccompound or inorganic compound as a light-emitting substance has beenactively developed. In particular, a light-emitting element called an ELelement having a simple structure in which a light-emitting layerincluding a light-emitting substance is provided between electrodes, hasattracted attention as a next-generation flat panel display elementbecause of its characteristics such as a thin shape, lightweight, highresponse speed, and direct current driving at a low voltage. Inaddition, a display using such a light-emitting element has a featurethat it is excellent in contrast and image quality, and has a wideviewing angle. Further, since such a light-emitting element is a planelight source, the light-emitting element is considered to be applicableto a light source such as a backlight of a liquid crystal display andlighting.

In a case of using a light-emitting organic compound as a light-emittingsubstance, the emission mechanism of a light-emitting element is acarrier-injection type. In other words, by application of voltage with alight-emitting layer interposed between electrodes, carriers (holes andelectrons) are injected from the electrodes to be recombined, and thus alight-emitting substance is excited. Light is emitted when the excitedstate returns to a ground state. There are two types of the excitedstates which are possible: a singlet excited state (S*) and a tripletexcited state (T*). In addition, the statistical generation ratiothereof in a light-emitting element is considered to be S*:T*=1:3.

In general, the ground state of a light-emitting organic compound is asinglet state. Light emission from a singlet excited state (S*) isreferred to as fluorescence where electron transition occurs between thesame multiplicities. On the other hand, light emission from a tripletexcited state (T*) is referred to as phosphorescence where electrontransition occurs between different multiplicities. Here, in general, atroom temperature, a compound capable of converting a singlet excitedstate into light emission (hereinafter referred to as a fluorescentcompound) does not exhibit light emission from the triplet excited state(phosphorescence) and exhibits only light emission from the singletexcited state (fluorescence). Accordingly, the internal quantumefficiency (the ratio of generated photons to injected carriers) in alight-emitting element using a fluorescent compound is assumed to have atheoretical limit of 25% based on S*:T*=1:3.

On the other hand, when a compound which converts an energy differencebetween a triplet excited state and a ground state (a triplet excitationenergy) into light emission and exhibits phosphorescence (hereinafterreferred to as a phosphorescent compound) is used, internal quantumefficiency can be theoretically 75% to 100%. In other words, emissionefficiency can be 3 to 4 times as much as that of the fluorescencecompound. From these reasons, in order to achieve a light-emittingelement with high efficiency, a light-emitting element using aphosphorescent compound has been proposed (see Non-Patent Document 1,for example). Note that in Non-Patent Document 1, an iridium complex isused, in which a ligand is 2-(2′-benzo[4,5-a]thienyl)pyridine([btp₂Ir(acac)]), as a phosphorescent compound.

The present inventors propose a light-emitting element using anorganometallic complex represented by Structural Formula (50) below,which is (acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium(III)(abbr.: [Ir(tppr)₂(acac)]) (Patent Document 1). By fabrication of alight-emitting element using the organometallic complex represented byStructural Formula (50), a light-emitting element which can exhibit redlight emission with high emission efficiency can be obtained.

REFERENCE Patent Document

[Patent Document 1]

Japanese Published Patent Application No. 2007-284432.

Non-Patent Document

[Non-Patent Document 1]

Adachi et al., HIGH-EFFICIENCY RED ELECTROPHOSPHORESCENCE DEVICES, APPL.PHYS. LETT. (APPLIED PHYSICS LETTERS), VOL. 78, NO. 11, March 2001, PP.1622-1624.

DISCLOSURE OF INVENTION

An organometallic complex disclosed in Non-Patent Document 1 emitsorange light; thus, when the organometallic complex is applied to afull-color display or the like, color purity of red is poor, which is adisadvantage in terms of color reproducibility. In contrast, in the casewhere the light emission color is in a dark red region, in other words,where the emission wavelength is extremely long, an organometalliccomplex is advantageous in terms of color reproducibility; however, in aregion of red light emission with low luminous efficiency (cd/A), theemission efficiency is decreased.

In view of the above problems, an object is to provide a light-emittingelement which exhibits red light emission with high luminous efficiency.In addition, another object is to provide a light-emitting elementhaving a light emission peak in the vicinity of 620 nm since the lightwhich perceived by a person as a favorable red light has a wave lengthof approximately 620 nm (preferably 620 nm to 625 nm). It is stillanother object to provide a light-emitting device and an electronicdevice with reduced power consumption.

SUMMARY OF THE INVENTION

One embodiment of a structure of the invention disclosed in thisspecification is a light-emitting element that includes, between a pairof electrodes, a layer including an organometallic complex representedby following General Formula (G1) and a low molecular compound. Theorganometallic complex is a guest material, and the low molecularcompound is a host material.

Note that, in the formula, R¹ to R¹⁵ individually represent hydrogen oran alkyl group having 1 to 4 carbon atoms. In addition, one of R²¹ andR²² represents an alkyl group having 2 to 10 carbon atoms and the otherrepresents an alkyl group having 1 to 10 carbon atoms. M is a centralmetal and represents either an element belonging to Group 9 or anelement belonging to Group 10. In addition, n is 2 when the centralmetal is an element belonging to Group 9, and n is 1 when the centralmetal is an element belonging to Group 10.

One embodiment of a structure of the invention disclosed in thisspecification is a light-emitting element that includes, between a pairof electrodes, a layer including an organometallic complex representedby following General Formula (G2) and a low molecular compound. Theorganometallic complex is a guest material, and the low molecularcompound is a host material.

Note that, in the formula, one of R²¹ and R²² represents an alkyl grouphaving 2 to 10 carbon atoms and the other represents an alkyl grouphaving 1 to 10 carbon atoms. M is a central metal and represents eitheran element belonging to Group 9 or an element belonging to Group 10. Inaddition, n is 2 when the central metal is an element belonging to Group9, and n is 1 when the central metal is an element belonging to Group10.

In order to obtain phosphorescence more efficiently from theorganometallic complex represented by above General Formula (G1) or(G2), a heavy metal is preferably used as a central metal in terms of aheavy atom effect. Thus, in the above organometallic complexes, onepreferable embodiment is an organometallic complex in which the centralmetal M is iridium or platinum. Particularly when the central metal M isiridium, thermal and chemical stability of the organometallic complex isimproved and morphology of a thin film becomes more stable. Thus,iridium is particularly preferable to be used as the central metal M.

A light-emitting element according to an embodiment of the presentinvention can realize high emission efficiency; accordingly, alight-emitting device (such as an image display device) using thislight-emitting element can realize low power consumption. Thus; anembodiment of the present invention includes a light-emitting device andan electronic device using the light-emitting element according to anembodiment of the present invention.

With the above structure, at least one of the above problems can beresolved.

Note that the light-emitting device in this specification includes imagedisplay devices and lighting devices using a light-emitting element.Further, the category of the light-emitting device includes a moduleincluding a light-emitting element attached with a connector such as amodule attached with an anisotropic conductive film, tape automatedbonding (TAB) tape, or a tape carrier package (TCP); a module in whichthe top of the TAB tape or the TCP is provided with a printed wiringboard; or a module in which an integrated circuit (IC) is directlymounted on a light-emitting element by a chip on glass (COG) method; andthe like.

By implementation of the present invention, a light-emitting elementwith high emission efficiency can be provided. In addition, the presentinvention can provide a light-emitting element with which red lightemission with high purity can be obtained.

Further, by manufacture of a light-emitting device using thelight-emitting element described above, a light-emitting device with lowpower consumption can be provided. In addition, by application of such alight-emitting device to an electronic device, an electronic device withlow power consumption and a long lifetime can be provided.

BRIEF DESCRIPTION OF THE DRAWINGS

In the accompanying drawings:

FIG. 1 illustrates a light-emitting element according to an embodimentof the present invention;

FIG. 2 illustrates a light-emitting element according to an embodimentof the present invention;

FIG. 3 illustrates a light-emitting element according to an embodimentof the present invention;

FIGS. 4A to 4C each illustrate a light-emitting device according to anembodiment of the present invention;

FIGS. 5A to 5E each illustrate an electronic device according to anembodiment of the present invention;

FIG. 6 illustrates lighting devices according to an embodiment of thepresent invention;

FIG. 7 shows a ¹H-NMR chart ofbis(2,3,5-triphenylpyrazinato)(2,2-dimethyl-3,5-hexanedionato)iridium(III);

FIG. 8 shows an absorption spectrum and an emission spectrum ofbis(2,3,5-triphenylpyrazinato)(2,2-dimethyl-3,5-hexanedionato)iridium(III);

FIG. 9 shows a ¹H-NMR chart ofbis(2,3,5-triphenylpyrazinato)(2,6-dimethyl-3,5-heptanedionato)iridium(III);

FIG. 10 shows an absorption spectrum and an emission spectrum ofbis(2,3,5-triphenylpyrazinato)(2,6-dimethyl-3,5-heptanedionato)iridium(III);

FIG. 11 shows a ¹H-NMR chart ofbis(2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III);

FIG. 12 shows an absorption spectrum and an emission spectrum ofbis(2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III);

FIG. 13 illustrates a light-emitting element according to Example 4;

FIG. 14 shows a graph of current density-luminance characteristics oflight-emitting elements 1 to 3 and a comparative light-emitting element1;

FIG. 15 shows a graph of voltage-luminance characteristics of thelight-emitting elements 1 to 3 and the comparative light-emittingelement 1;

FIGS. 16A and 16B show emission spectra of the light-emitting elements 1to 3 and the comparative light-emitting element 1;

FIG. 17 illustrates a light-emitting element according to Example 5;

FIG. 18 shows a graph of current density-luminance characteristics of alight-emitting element 4 and a comparative light-emitting element 2;

FIG. 19 shows a graph of voltage-luminance characteristics of thelight-emitting element 4 the comparative light-emitting element 2;

FIG. 20 shows emission spectra of the light-emitting element 4 and thecomparative light-emitting element 2;

FIG. 21 shows results obtained by reliability tests of thelight-emitting elements 1 to 3 and the comparative light-emittingelement 1;

FIG. 22 shows results obtained by reliability tests of thelight-emitting element 4 and the comparative light-emitting element 2;

FIG. 23 shows a ¹H-NMR chart ofbis(5-phenyl-2,3-di-m-tolylpyrazinato)(dipivaloylmethanato)iridium(III);

FIG. 24 shows an absorption spectrum and an emission spectrum ofbis(5-phenyl-2,3-di-m-tolylpyrazinato)(dipivaloylmethanato)iridium(III);and

FIG. 25 shows sublimation properties of bis(2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III) and(acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium(III).

DETAILED DESCRIPTION OF THE INVENTION

Hereinafter, embodiments of the present invention are described withreference to the accompanying drawings. Note that the inventiondisclosed in this specification is not limited to the followingdescription because it will be easily understood by those skilled in theart that various changes and modifications can be made without departingfrom the spirit and scope of the present invention. Accordingly, thepresent invention is not to be taken as being limited to the describedcontent of the embodiments included herein. In the drawings forexplaining the embodiments, the same parts or parts having a similarfunction are denoted by the same reference numerals, and description ofsuch parts is not repeated.

Embodiment 1

In this embodiment, an organometallic complex used for a light-emittingelement is described.

One embodiment of the light-emitting element disclosed in thisspecification is a light-emitting element including an organometalliccomplex represented by following General Formula (G1).

Note that, in the formula, R¹ to R¹⁵ individually represent hydrogen oran alkyl group having 1 to 4 carbon atoms. In addition, one of R²¹ andR²² represents an alkyl group having 2 to 10 carbon atoms and the otherrepresents an alkyl group having 1 to 10 carbon atoms. M is a centralmetal and represents either an element belonging to Group 9 or anelement belonging to Group 10. In addition, n is 2 when the centralmetal is an element belonging to Group 9, and n is 1 when the centralmetal is an element belonging to Group 10.

In addition, the organometallic complex represented by General Formula(G1) is preferably an organometallic complex represented by followingGeneral Formula (G2).

Note that one of R²¹ and R²² represents an alkyl group having 2 to 10carbon atoms and the other represents an alkyl group having 1 to 10carbon atoms. M is a central metal and represents either an elementbelonging to Group 9 or an element belonging to Group 10. In addition, nis 2 when the central metal is an element belonging to Group 9, and n is1 when the central metal is an element belonging to Group 10.

Specific examples of an organometallic complex to be used for alight-emitting element can be organometallic complexes represented byStructural Formulae (10) to (44). Note that an organometallic complexused for the light-emitting element is not limited thereto.

An example of a synthesis method of the organometallic complexrepresented by General Formula (G1) is described hereinafter.

First, as shown in a following synthesis scheme (a-1), the pyrazinederivative represented by General Formula (G0) and a metal compoundincluding a metal belonging to Group 9 or Group 10 and including halogen(such as a metal halide or metal complex) are heated in an appropriatesolvent to obtain a binuclear complex (A) which is a kind oforganometallic complexes having the structure represented by GeneralFormula (G1). A metal compound including a metal belonging to Group 9 orGroup 10 and including halogen is, for example, rhodium chloridehydrate, palladium chloride, iridium chloride hydrate, iridium chloridehydrochloride hydrate, potassium tetrachloroplatinate(II), or the like.Note that in the synthesis scheme (a-1), M represents an elementbelonging to Group 9 or an element belonging to Group 10, and Xrepresents a halogen element. In addition, n is 2 when M is an elementbelonging to Group 9, and n is 1 when M is an element belonging to Group10. In addition, R¹ to R¹⁵ individually represent hydrogen or an alkylgroup having 1 to 4 carbon atoms.

Next, as shown in a following synthesis scheme (a-2), the binuclearcomplex (A) obtained by the synthesis scheme (a-1) reacts with amonoanionic bidentate chelate ligand having a β-diketone structure and aproton of the ligand is separated to be coordinated to the central metalM. As a result, the organometallic complex represented by GeneralFormula (G1) is obtained.

Note that, in the synthesis scheme (a-2), M represents an elementbelonging to Group 9 or Group 10 and X represents a halogen element. Inaddition, n is 2 when M is an element belonging to Group 9, and n is 1when M is an element belonging to Group 10. In addition, R¹ to R¹⁵individually represent hydrogen or an alkyl group having 1 to 4 carbonatoms. Note that one of R²¹ and R²² represents an alkyl group having 2to 10 carbon atoms and the other represents an alkyl group having 1 to10 carbon atoms.

The above-described organometallic complex represented by GeneralFormula (G1) has a light emission peak in the vicinity of 620 nm, andexhibits a favorable red light emission with high luminous efficiency.Thus, by applying the organometallic complex described in thisembodiment to a light-emitting element, a light-emitting element whichexhibits red light emission with high luminous efficiency can beobtained.

The above-described organometallic complex is a substance which islikely to sublime at a low temperature. Specifically, in this substance,when a measurement is conducted under a low pressure of approximately10⁻³ Pa, the temperature at which the weight is reduced by 5% from theweight at the start of the measurement (hereinafter also referred to as5% weight loss temperature) is 250° C. or lower in terms of the relationbetween the weight and temperature using a high vacuum differential typedifferential thermal balance. Thus, since the substance can sublimewithout pyrolysis, a light-emitting layer is formed by an evaporationmethod, and it can be avoided that decomposed matters are mixed in thelight-emitting layer.

In addition, since the organometallic complex according to thisembodiment can exhibit phosphorescence, in other words, it can converttriplet excitation energy into light emission, with the application ofthe organometallic complex to a light-emitting element, high efficiencycan be achieved. Note that the organometallic complex according to thisembodiment is effective when it is used for a light-emitting substancein terms of emission efficiency. In addition, the light-emitting elementpreferably includes a light-emitting layer between a pair of electrodes,and the light-emitting layer preferably has a structure in which theorganometallic complex according to this embodiment is dispersed in ahost material.

Note that, in the organometallic complexes represented by GeneralFormulae (G1) and (G2), it is preferable that both R²¹ and R²² are alkylgroups each having 2 to 4 carbon atoms, more preferably, 3 to 4 carbonatoms. When a light-emitting element is manufactured using theorganometallic complex represented by General Formula (G1) or (G2) inwhich both R²¹ and R²² fall in the above ranges, the operation voltageof the light-emitting element can be low.

Embodiment 2

In this embodiment, one embodiment of a light-emitting element isdescribed with reference to FIG. 1.

A light-emitting element including a light-emitting layer 113 between afirst electrode 101 and a second electrode 102 is illustrated in FIG. 1.Note that the first electrode 101 and the second electrode 102 serve asan anode and a cathode, respectively, in the light-emitting element ofEmbodiment 2. When voltage is applied to the first electrode 101 and thesecond electrode 102 so that a potential of the first electrode 101 ishigher than that of the second electrode 102, holes are injected fromthe side of the first electrode 101, and electrons are injected from theside of the second electrode 102 to the light-emitting layer 113.Subsequently, holes and electrons injected to the light-emitting layer113 are recombined. A light-emitting substance is included in thelight-emitting layer 113, and the light-emitting substance becomesexcited due to excitation energy generated by the recombination. Theexcited light-emitting substance emits light while returning to a groundstate.

In addition, a hole-transporting layer 112 may be provided between thefirst electrode 101 and the light-emitting layer 113. Here, ahole-transporting layer is a layer which has a function of transportingholes injected from the first electrode 101 to the light-emitting layer113. In such a manner, since the hole-transporting layer 112 is providedso as to separate the first electrode 101 from the light-emitting layer113, quenching light emission due to a metal can be prevented. Note thatthe hole-transporting layer 112 is not necessarily provided.

Here, the light-emitting layer 113 includes an organometallic complexhaving the structure represented by General Formula (G1). Thelight-emitting layer 113 preferably includes a substance that has largertriplet excitation energy than the organometallic complex described inEmbodiment 1 as a host and also includes the organometallic complexdescribed in Embodiment 1, which is dispersed as a guest material. Thus,quenching of light emitted from the organometallic complex causeddepending on the concentration can be prevented. Note that the tripletexcited energy indicates an energy gap between a ground state and atriplet excited state.

Although there is no particular limitation on a method for forming thelight-emitting layer 113, an evaporation method is preferably used. In acase where the light-emitting layer 113 is formed by an evaporationmethod, a shadow mask technique can be used when the light-emittinglayer 113 is patterned; thus, minute patterning can be performed on thelight-emitting layer. In addition, since the light-emitting layer can beformed in vacuum by a dry process, the purity of light-emittingmaterials can be kept.

There is no particular limitation on a substance (i.e., a host material)used for dispersing the organometallic complex described in Embodiment1; however, it is preferable to use a compound having an arylamineskeleton such as 2,3-bis(4-diphenylaminophenyl)quinoxaline (abbr.:TPAQn) or 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbr.: NPB), acarbazole derivative such as 4,4′-di(N-carbazolyl)biphenyl (abbr.: CBP)or 4,4′,4″-tris(N-carbazolyl)triphenylamine (abbr.: TCTA), or a metalcomplex such as bis[2-(2-hydroxyphenyl)pyridinato]zinc (abbr.: Znpp₂),bis[2-(2-hydroxyphenyl)benzoxazolato]zinc (abbr.: ZnBOX),bis(2-methyl-8-quinolinolato)(4-phenyphenolato)aluminum (abbr.: BAlq) ortris(8-quinolinolato)aluminum (abbr.: Alq₃). One or more of thesematerials can be selected to be mixed so that the organometallic complexdescribed in Embodiment 1 becomes dispersed. Note that in a case wherethe light-emitting layer 113 is formed by an evaporation method, a lowmolecular compound is preferably used as the host material. The lowmolecular compound in this specification refers to a compound whosemolecular weight is greater than or equal to 100 and less than or equalto 2000, preferably greater than or equal to 100 and less than or equalto 1500. In addition, in a case where a plurality of compounds are mixedto form the light-emitting layer 113, a co-evaporation method can beused. Here, the co-evaporation method refers to an evaporation method inwhich raw materials from a plurality of evaporation sources provided ina single treatment chamber are each vaporized, the vaporized rawmaterials are mixed in a gaseous state, and then deposited over atreatment object.

Since the organometallic complex described in Embodiment 1 can emit afavorable red light, a light-emitting element which emits red light canbe provided. In addition, since the organometallic complex described inEmbodiment 1 exhibits phosphorescence, the emission efficiency is high.Accordingly, by using the organometallic complex for the light-emittinglayer, a light-emitting element with high emission efficiency can beobtained. Furthermore, a light-emitting element which emits red lightwith high luminous efficiency (cd/A) can be provided because the lightemission peak is in the vicinity of 620 nm.

The organometallic complex described in Embodiment 1 has a lowsublimation temperature; thus, it can sublime without pyrolysis.Accordingly, in a case where a light-emitting layer is formed by anevaporation method, gas or decomposed matters which are generated bydecomposition of evaporation materials can suppress reduction in thedegree of vacuum in the evaporation atmosphere, and the decomposedmatters can be prevented from being mixed in the light-emitting layer.

In addition, because the light-emitting element described in thisembodiment has high emission efficiency, the power consumption can bereduced.

Further, although there is no particular limitation on the firstelectrode 101, it is preferably formed using a substance having a highwork function to enable it to serve as an anode, as in this embodiment.Specifically, it is possible to use indium tin oxide (ITO), indium tinoxide containing silicon oxide (ITSO), indium oxide containing zincoxide at 2 to 20 wt % (IZO), gold (Au), platinum (Pt), nickel (Ni),tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co),copper (Cu), palladium (Pd), or the like. Note that the first electrode101 can be formed, for example, by a sputtering method, an evaporationmethod, or the like.

Furthermore, although there is no particular limitation on the secondelectrode 102, it is preferably formed using a substance having a lowwork function to enable it to serve as a cathode, as in this embodiment.Specifically, it is possible to use aluminum (Al), indium (In), analkali metal such as lithium (Li) or cesium (Cs), an alkaline-earthmetal such as magnesium (Mg) or calcium (Ca), a rare-earth metal such aserbium (Er) or ytterbium (Yb), or the like. Alternatively, an alloy suchas aluminum-lithium alloy (AILi) or magnesium-silver alloy (MgAg) can beused. Note that the second electrode 102 can be formed by, for example,a sputtering method, an evaporation method, or the like.

Note that in order to extract emitted light to the outside, it isnecessary that either or both the first electrode 101 or/and the secondelectrode 102 be an electrode formed using a conductive film that cantransmit visible light, such as ITO, or an electrode with a thickness ofseveral to several tens of nanometers so as to transmit visible light.

Although there is no particular limitation on a substance included inthe hole-transporting layer 112, for example, it is possible to use anaromatic amine compound such as4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbr.: NPB),4,4′-bis[N-(3-methylphenyl)-N-phenylamino]biphenyl (abbr.: TPD),4,4′-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbr.:DFLDPBi), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (abbr.: TDATA),or 4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbr.:m-MTDATA), or a high molecular compound such as poly(4-vinyltriphenylamine) (abbr.: PVTPA).

Note that the hole-transporting layer 112 may have a multilayerstructure in which two or more layers are stacked. In addition, thehole-transporting layer 112 may also be formed by mixing two or moretypes of substances.

Further, as illustrated in FIG. 1, an electron-transporting layer 114may be provided between the second electrode 102 and the light-emittinglayer 113. Here, the electron-transporting layer refers to a layerhaving the function of transporting electrons injected from the secondelectrode 102 to the light-emitting layer 113. By thus providing theelectron-transporting layer 114 so as to separate the second electrode102 from the light-emitting layer 113, quenching of emitted light due tometal can be prevented. Note that the electron-transporting layer 114 isnot necessarily provided.

Although there is no particular limitation on a substance forming theelectron-transporting layer 114, for example, it is possible to use ametal complex such as tris(8-quinolinolato)aluminum (abbr.: Alq₃),tris(4-methyl-8-quinolinolato)aluminum (abbr.: Almq₃),bis(10-hydroxybenzo[h]quinolinato)beryllium (abbr.: BeBq₂),bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum (abbr.: BAlq),bis[2-(2-hydroxyphenyl)benzoxazolato]zinc (abbr.: ZnBOX), orbis[2-(2-hydroxyphenyl)benzothiazolato]zinc (abbr.: Zn(BTZ)₂), aheteroaromatic compound such as2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbr.: PBD),1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbr.:OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole(abbr.: TAZ),3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole(abbr.: p-EtTAZ), bathophenanthroline (abbr.: BPhen), bathocuproine(abbr.: BCP), or 4,4′-bis(5-methylbenzoxazol-2-yl)stilbene (abbr.:BzOs), or a high molecular compound such as poly(2,5-pyridine-diyl)(abbr.: PPy).

Note that the electron-transporting layer 114 may have a multilayerstructure in which two or more layers are stacked. In addition, theelectron-transporting layer 114 may also be formed by mixing two or moretypes of substances.

Further, as illustrated in FIG. 1, a hole-injecting layer 111 may beprovided between the first electrode 101 and the hole-transporting layer112. Here, the hole-injecting layer refers to a layer having a functionof assisting injection of holes from an electrode serving as an anode tothe hole-transporting layer 112. Note that the hole-injecting layer 111is not necessarily provided.

Although there is no particular limitation on a substance forming thehole-injecting layer 111, for example, it is possible to use metal oxidesuch as vanadium oxide, niobium oxide, tantalum oxide, chromium oxide,molybdenum oxide, tungsten oxide, manganese oxide, rhenium oxide, andruthenium oxide, a phthalocyanine compound such as phthalocyanine(abbr.: H₂Pc), copper phthalocyanine (abbr.: CuPc), or the like.Alternatively, any of the substances for forming the hole-transportinglayer 112 as described above can also be used. Further alternatively, ahigh molecular compound such as a mixture ofpoly(ethylenedioxythiophene) and poly(styrene sulfonate) (abbr.:PEDOT/PSS) can be used.

Still alternatively, for the hole-injecting layer 111, a compositematerial formed by combining an organic compound and an electronacceptor may be used. Such a composite material is superior in ahole-injecting property and a hole-transporting property, since holesare generated in the organic compound by the electron acceptor. In thiscase, the organic compound is preferably a material excellent intransporting the generated holes. Specifically, the above-describedsubstances for forming the hole-transporting layer 112 (e.g., anaromatic amine compound) can be used for example. As the electronacceptor, a substance having an electron-accepting property to theorganic compound may be used. Specifically, transition metal oxide ispreferable and examples thereof include vanadium oxide, niobium oxide,tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide,manganese oxide, rhenium oxide, ruthenium oxide, and the like. Lewisacid such as iron chloride(III) or aluminum chloride(III) can also beused. Alternatively, an organic compound such as7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbr.: F₄-TCNQ)can also be used.

Note that the hole-injecting layer 111 may have a multilayer structurein which two or more layers are stacked. In addition, the hole-injectinglayer 111 may also be formed by mixing two or more types of substances.

Further, as illustrated in FIG. 1, an electron-injecting layer 115 mayalso be provided between the second electrode 102 and theelectron-transporting layer 114. Here, the electron-injecting layerrefers to a layer which has the function of assisting injection ofelectrons from the electrode serving as a cathode to theelectron-transporting layer 114. Note that the electron-injecting layer115 is not necessarily provided.

Although there is no particular limitation on a substance forming theelectron-injecting layer 115, for example, it is possible to use analkali metal compound or an alkaline-earth metal compound such aslithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF₂),or lithium oxide and a rare earth metal compound such as erbium fluoride(ErF₃). Alternatively, the above-mentioned substances for forming theelectron-transporting layer 114 can also be used.

Alternatively, for the electron-injecting layer 115, a compositematerial formed by combining an organic compound and an electron donormay be used. The composite material is superior in an electron-injectingproperty and an electron-transporting property, since electrons aregenerated in the organic compound by the electron donor. In this case,the organic compound is preferably a material excellent in transportingthe generated electrons. Specifically, the above-described materials forforming the electron-transporting layer 114 (e.g., a metal complex or aheteroaromatic compound) can be used for example. As the electron donor,a substance exhibiting an electron-donating property to the organiccompound may be used, and it is preferable to use an alkali metal, analkaline-earth metal, or a rare earth metal, such as lithium, cesium,magnesium, calcium, erbium, or ytterbium. Further, it is also preferableto use an alkali metal oxide or an alkaline-earth metal oxide, such aslithium oxide (LiOx), calcium oxide (CaOx), or barium oxide (BaOx).Alternatively, Lewis acid such as magnesium oxide can also be used.Further alternatively, an organic compound such as tetrathiafulvalene(abbr.: TTF) can be used.

In the above-described light-emitting element described in thisembodiment, each the hole-injecting layer 111, the hole-transportinglayer 112, the light-emitting layer 113, the electron-transporting layer114, and the electron-injecting layer 115 may be formed by any method,for example, an evaporation method, an inkjet method, an applicationmethod, or the like. In addition, each the first electrode 101 and thesecond electrode 102 may also be formed by any of a sputtering method,an evaporation method, an inkjet method or an application method.

Note that this embodiment can be implemented in free combination withany of the other embodiments.

Embodiment 3

In Embodiment 3, an example of an embodiment of a light-emitting elementwhich is different from that of Embodiment 2 is described with referenceto FIG. 2. The light-emitting element using an organometallic complexdescribed in Embodiment 1 may have a plurality of light-emitting layers.For example, by providing a plurality of light-emitting layers, lightwhich is a combination of the light emitted from the plurality of layerscan be obtained. Thus, white light emission can be obtained, forexample. In Embodiment 3, an embodiment of a light-emitting elementhaving a plurality of light-emitting layers is described with referenceto FIG. 2.

In FIG. 2, a first light-emitting layer 213 and a second light-emittinglayer 215 are provided between a first electrode 201 and a secondelectrode 202. Light which is a combination of light emitted from thefirst light-emitting layer 213 and light emitted from the secondlight-emitting layer 215 can be obtained. A separation layer 214 ispreferably formed between the first light-emitting layer 213 and thesecond light-emitting layer 215.

When voltage is applied so that a potential of the first electrode 201is higher than a potential of the second electrode 202, current flowsbetween the first electrode 201 and the second electrode 202, and holesand electrons are recombined in the first light-emitting layer 213, thesecond light-emitting layer 215, or the separation layer 214. Generatedexcitation energy is distributed to both the first light-emitting layer213 and the second light-emitting layer 215 to excite a firstlight-emitting substance included in the first light-emitting layer 213and a second light-emitting substance included in the secondlight-emitting layer 215. The excited first and second light-emittingsubstances emit light while returning to the ground state.

The first light-emitting layer 213 includes the first light-emittingsubstance typified by a fluorescent compound such as perylene,2,5,8,11-tetra(tert-butyl)perylene (abbr.: TBP),4,4′-bis(2,2-diphenylvinyl)biphenyl (abbr.: DPVBi),4,4′-bis[2-(N-ethylcarbazol-3-yl)vinyl]biphenyl (abbr.: BCzVBi),bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum (abbr.: BAlq),or bis(2-methyl-8-quinolinolato)galliumchloride (abbr.: Gamq₂Cl), or aphosphorescent substance such asbis{2-[3,5-bis(trifluoromethyl)phenyl]pyridinato-N,C^(2′)}iridium(III)picolinate(abbr.: Ir(CF₃ppy)₂(pic)),bis[2-(4,6-difluorophenyl)pyridinato-N,C^(2′)]iridium(III)acetylacetonate (abbr.: FIr(acac)),bis[2-(4,6-difluorophenyl)pyridinato-N,C^(2′)]iridium(III)picolinate(abbr.: FIrpic), orbis[2-(4,6-difluorophenyl)pyridinato-N,C^(2′)]iridium(III)tetra(1-pyrazolyl)borate(abbr.: FIr6), from which light emission with a peak at 450 nm to 510 nmin an emission spectrum (i.e., blue light to blue green light) can beobtained. In addition, when the first light-emitting substance is afluorescent compound, the first light-emitting layer 213 preferably hasa structure in which a substance that has larger singlet excitationenergy than the first light-emitting substance is used as a first hostand the first light-emitting substance is dispersed as a guest. Further,when the first light-emitting substance is a phosphorescent compound,the first light-emitting layer 213 preferably has a structure in which asubstance that has larger triplet excitation energy than the firstlight-emitting substance is used as a first host and the firstlight-emitting substance is dispersed as a guest. As the first host,9,10-di(2-naphthyl)anthracene (abbr.: DNA),2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbr.: t-BuDNA) or the likecan be used as well as NPB, CBP, TCTA or the like. Note that the singletexcitation energy is an energy difference between a ground state and asinglet excited state. In addition, the triplet excitation energy is anenergy difference between a ground state and a triplet excited state.

On the other hand, the second light-emitting layer 215 includes any ofthe organometallic complexes described in Embodiment 1 and can emit redlight. Further, since any of the organometallic complexes described inEmbodiment 1 has high emission efficiency, a light-emitting element withhigh emission efficiency can be obtained. In addition, a light-emittingelement with reduced power consumption can be obtained.

The second light-emitting layer 215 may have a structure similar to thatof the light-emitting layer 113 described in Embodiment 2.

Specifically, the separation layer 214 can be formed using TPAQn, NPB,CBP, TCTA, Znpp₂, ZnBOX or the like described above. By thus providingthe separation layer 214, a defect that emission intensity of one of thefirst light-emitting layer 213 and the second light-emitting layer 215is stronger than that of the other can be prevented. Note that theseparation layer 214 is not necessarily provided, and it may be providedas appropriate so that the ratio in emission intensity of the firstlight-emitting layer 213 and the second light-emitting layer 215 can beadjusted.

Note that in Embodiment 3, any of the organometallic complexes describedin Embodiment 1 is used for the second light-emitting layer 215, andanother light-emitting substance is used for the first light-emittinglayer 213; however, any of the organometallic complexes described inEmbodiment 1 may be used for the first light-emitting layer 213, andanother light-emitting substance may be used for the secondlight-emitting layer 215.

Further, in Embodiment 3, a light-emitting element including twolight-emitting layers is described as illustrated in FIG. 2; however,the number of the light-emitting layers is not limited to two, and maybe more than two, for example, three as long as light emission from eachlight-emitting layer can be mixed. As a result, white light emission canbe obtained, for example.

Note that the first electrode 201 may have a structure similar to thatof the first electrode 101 described in Embodiment 2. Further, thesecond electrode 202 may also have a structure similar to that of thesecond electrode 102 described in Embodiment 2.

Further, in Embodiment 3, as illustrated in FIG. 2, a hole-injectinglayer 211, a hole-transporting layer 212, an electron-transporting layer216, and an electron-injecting layer 217 are provided. The structures ofthe respective layers described in Embodiment 2 may be applied to theselayers. However, these layers are not necessarily provided and may beprovided as appropriate according to element characteristics.

Note that this embodiment can be implemented in free combination withany of the other embodiments.

Embodiment 4

In Embodiment 4, a light-emitting element in which a plurality oflight-emitting layers are provided and light is emitted from theselayers with a different element structure from that in Embodiment 3 isexemplified. Accordingly, also in Embodiment 4, light which is acombination of light emitted from the plurality of layers can beobtained. In other words, white light can be obtained. Hereinafter,description is made with reference to FIG. 3.

In the light-emitting element in FIG. 3, a first light-emitting layer313 and a second light-emitting layer 323 are provided between a firstelectrode 301 and a second electrode 302. An N layer 315 and a P layer321 as charge-generating layers are provided between the firstlight-emitting layer 313 and the second light-emitting layer 323.

The N layer 315 is a layer for generating electrons, and the P layer 321is a layer for generating holes. When voltage is applied so that apotential of the first electrode 301 is higher than that of the secondelectrode 302, holes injected from the first electrode 301 and electronsinjected from the N layer 315 are recombined in the first light-emittinglayer 313, and thus, a first light-emitting substance included in thefirst light-emitting layer 313 emits light. Further, electrons injectedfrom the second electrode 302 and holes injected from the P layer 321are recombined in the second light-emitting layer 323, and thus, asecond light-emitting substance included in the second light-emittinglayer 323 emits light.

The first light-emitting layer 313 may have a structure similar to thatof the first light-emitting layer 213 of Embodiment 3, and light with apeak of emission spectrum at 450 nm to 510 nm (i.e., blue light to bluegreen light) can be obtained. The second light-emitting layer 323 mayhave the same structure as the second light-emitting layer 215 inEmbodiment 3, and includes an organometallic complex described inEmbodiment 1 and red light emission can be obtained. Since theorganometallic complex described in Embodiment 1 has high emissionefficiency, a light-emitting element with high emission efficiency canbe obtained. In addition, a light-emitting element with reduced powerconsumption can be obtained.

Since the N layer 315 is a layer for generating electrons, it may beformed using a composite material in which the organic compound and theelectron donor described in Embodiment 2 are combined. By adopting sucha structure, electrons can be injected to the first light-emitting layer313 side.

The P layer 321 is a layer for generating holes, and thus, may be formedusing a composite material in which the organic compound and theelectron donor described in Embodiment 2 are combined. By adopting sucha structure, holes can be injected to the second light-emitting layer323 side. For the P layer 321, metal oxide having an excellenthole-injecting property, such as molybdenum oxide, vanadium oxide, ITO,or ITSO, can be used.

Further, in Embodiment 3, a light-emitting element including twolight-emitting layers is described as illustrated in FIG. 3; however,the number of the light-emitting layers is not limited to two, and maybe more than two, for example, three as long as light emission from eachlight-emitting layer may be mixed. As a result, white light emission canbe obtained, for example.

The first electrode 301 may have a structure similar to the firstelectrode 101 described above in Embodiment 2. The second electrode 302may also have a structure similar to the second electrode 102 describedabove in Embodiment 2.

In Embodiment 4, as illustrated in FIG. 3, a hole-injecting layer 311,hole-transporting layers 312 and 322, electron-transporting layers 314and 324, and an electron-injecting layer 325 are provided. Thestructures of the respective layers described in Embodiment 2 may alsobe applied. However, these layers are not necessarily provided and maybe provided as appropriate according to element characteristics.

Note that this embodiment can be implemented in free combination withany of the other embodiments.

Embodiment 5

In Embodiment 5, an embodiment of a light-emitting element using any ofthe organometallic complexes described in Embodiment 1 as a sensitizeris described with reference to FIG. 1.

A light-emitting element including a light-emitting layer 113 between afirst electrode 101 and a second electrode 102 is illustrated in FIG. 1.The light-emitting layer 113 includes the organometallic complexdescribed in Embodiment 1, and a fluorescent compound which can emitlight with a longer wavelength than the organometallic complex.

In the light-emitting element like this, holes injected from the firstelectrode 101 and electrons injected from the second electrode 102 arerecombined in the light-emitting layer 113 to bring the fluorescentcompound to an excited state. The excited fluorescent compound emitslight while returning to the ground state. In this case, theorganometallic complex described in Embodiment 1 serves as a sensitizerfor the fluorescent compound to make more molecules of the fluorescentcompound be in the singlet excited state. From the above, alight-emitting element with high emission efficiency can be obtained byusing the organometallic complex described in Embodiment 1 as asensitizer. Note that the first electrode 101 and the second electrode102 serve as an anode and a cathode, respectively, in the light-emittingelement of Embodiment 5.

Here, the light-emitting layer 113 includes the organometallic complexdescribed in Embodiment 1, and a fluorescent compound which can emitlight with a longer wavelength than the organometallic complex. Thelight-emitting layer 113 preferably has a structure in which a substancehaving larger triplet excitation energy than the organometallic complexdescribed in Embodiment 1 and larger singlet excitation energy than thatof the fluorescent compound is used as a host, and the organometalliccomplex described in Embodiment 1 and the fluorescent compound aredispersed as a guest.

There is no particular limitation on the substance used for dispersingthe organometallic complex described in Embodiment 1 and the fluorescentcompound (i.e., host), and the substances given above as examples of thehost in Embodiment 2, or the like can be used.

In addition, there is also no particular limitation on the fluorescentcomplex; however, a compound which can exhibit emission of red light toinfrared light is preferable; for example,4-dicyanomethylene-2-isopropyl-6-[2-(1,1,7,7-tetramethyljulolidin-9-yl)-ethenyl]-4H-pyran(abbr.: DCJTI), magnesium phthalocyanine, magnesium porphyrin,phthalocyanine and the like are preferable.

The first electrode 101 and the second electrode 102 may have structuressimilar to those described in Embodiment 2.

In Embodiment 5, as illustrated in FIG. 1, the hole-injecting layer 111,the hole-transporting layer 112, the electron-transporting layer 114,and the electron-injecting layer 115 are provided. The structures of therespective layers described in Embodiment 2 may be applied. However,these layers are not necessarily provided and may be provided asappropriate according to element characteristics.

The above-described light-emitting element can emit light highlyefficiently by using the organometallic complex described in Embodiment1 as a sensitizer.

Note that this embodiment can be implemented in free combination withany of the other embodiments.

Embodiment 6

In Embodiment 6, one embodiment of light-emitting devices each includingany of the light-emitting elements described in the above embodiments isdescribed with reference to FIGS. 4A to 4C. FIGS. 4A to 4C arecross-sectional views illustrating the light-emitting devices.

In FIGS. 4A to 4C, a portion surrounded by dotted lines of a rectangularshape is a transistor 11 which is provided to drive a light-emittingelement 12. The light-emitting element 12 includes a layer 15 in which alight-emitting layer is formed between a first electrode 13 and a secondelectrode 14, and the light-emitting layer includes the organometalliccomplex described in Embodiment 1. Specifically, the light-emittingelement 12 has the structure as described in Embodiments 2 to 5. A drainregion of the transistor 11 is electrically connected to the firstelectrode 13 with a wiring 17 penetrating a first interlayer insulatingfilm 16 (16 a, 16 b, and 16 c). The light-emitting element 12 isseparated from other adjacently-provided light-emitting elements by apartition layer 18. The light-emitting device of this embodiment havingsuch a structure is provided over a substrate 10 in this embodiment.

The transistors 11 illustrated in FIGS. 4A to 4C each are a top gatetype in which a gate electrode is provided on a side opposite to asubstrate, regarding the semiconductor layer as a center. Note thatthere is no particular limitation on the structure of the transistor 11;for example, a bottom gate type may be used. In the case of a bottomgate type, the transistor 11 may have a structure in which a protectivefilm is formed over a semiconductor layer for forming a channel (achannel protective type) or a structure in which part of thesemiconductor layer for forming a channel has a depression (a channeletch type).

In addition, the semiconductor layer included in the transistor 11 maybe either crystalline or amorphous. Alternatively, the semiconductorlayer may be formed using a microcrystalline semiconductor, an oxidesemiconductor, or the like.

A composite oxide of an element selected from indium, gallium, aluminum,zinc, and tin can be used for the oxide semiconductor layer. Examplesinclude zinc oxide (ZnO), indium oxide containing zinc oxide (IZO), andoxide containing indium oxide, gallium oxide, and zinc oxide (IGZO). Inaddition, specific examples of the crystalline semiconductor layerinclude a layer formed using single-crystal or polycrystalline silicon,silicon germanium, or the like. The above examples may be formed bylaser crystallization or may be formed by crystallization through asolid-phase growth method using, for example, nickel.

In the case of using an amorphous substance, for example, amorphoussilicon for forming the semiconductor layer, it is preferable that thelight-emitting device have a circuit in which the transistor 11 andother transistors (transistors included in a circuit for driving thelight-emitting element) are all n-channel transistors. Many oxidesemiconductors such as zinc oxide (ZnO), indium oxide containing zincoxide (IZO), oxide containing indium oxide, gallium oxide, and zincoxide (IGZO), and the like are n-type semiconductors; therefore, atransistor which includes any of these compounds in an active layer isan n-channel transistor. Other than that case, the light-emitting devicemay have a circuit including either n-channel transistors or p-channeltransistors, or may have a circuit including both n-channel transistorsand p-channel transistors.

The first interlayer insulating films 16 a to 16 c may have a multilayerstructure as illustrated in FIGS. 4A and 4C, or a single-layerstructure. Note that the interlayer insulating film 16 a is formed usingan inorganic material such as silicon oxide or silicon nitride; theinterlayer insulating film 16 b is formed using acrylic, siloxane (anorganic group including a skeleton formed by a bond of silicon (Si) andoxygen (O) and including at least hydrogen as a substituent) or aself-planarizing substance which can be formed by an application method,such as silicon oxide. In addition, the interlayer insulating film 16 cis formed using a silicon nitride film including argon (Ar). Note thatthere is no particular limitation on materials forming each layer, and amaterial other than the above-described materials may also be used. Alayer formed using a material other than the above-described materialsmay be further combined. As described above, the first interlayerinsulating films 16 a to 16 c may be formed using either an inorganicmaterial or an organic material, or both of them.

The partition layer 18 preferably has a shape in an edge portion, inwhich a curvature radius changes continuously. In addition, acrylic,siloxane, resist, silicon oxide or the like is used to form thepartition layer 18. Note that the partition layer 18 may be formed usingeither an inorganic material or an organic material, or both of them.

In FIGS. 4A and 4C, only the first interlayer insulating films 16 a to16 c are provided between the transistor 11 and the light-emittingelement 12. However, as illustrated in FIG. 4B, a second interlayerinsulating film 19 (19 a and 19 b) may also be provided in addition tothe first interlayer insulating film 16 (16 a and 16 b). In thelight-emitting device illustrated in FIG. 4B, the first electrode 13penetrates the second interlayer insulating film 19 and is connected tothe wiring 17.

The second interlayer insulating film 19 may have a multilayer structureor a single-layer structure like the first interlayer insulating film16. The second interlayer insulating film 19 a is formed using acrylic,siloxane (an organic group including a skeleton formed by a bond ofsilicon (Si) and oxygen (O) and including at least hydrogen as asubstituent) or a self-planarizing substance which can be formed by anapplication method, such as silicon oxide. The second interlayerinsulating film 19 b is formed using a silicon nitride film includingargon (Ar). Note that there is no particular limitation on materialsforming each layer, and a material other than the above-describedmaterials may also be used. A layer formed using a material other thanthe above-described materials may be further combined. As describedabove, the second interlayer insulating film 19 may be formed usingeither an inorganic material or an organic material, or both of them.

When both the first electrode 13 and the second electrode 14 are formedusing light-transmitting substances in the light-emitting element 12,light emission can be extracted from both the first electrode 13 sideand the second electrode 14 side as indicated by the outlined arrows inFIG. 4A. When only the second electrode 14 is formed using alight-transmitting substance, light emission can be extracted from onlythe second electrode 14 side as indicated by the outlined arrow in FIG.4B. In this case, it is preferable to form the first electrode 13 usinga highly reflective material or to provide a film formed from a highlyreflective material (reflective film) below the first electrode 13. Whenonly the first electrode 13 is formed using a light-transmittingsubstance, light emission can be extracted from only the first electrode13 side as indicated by the outlined arrow in FIG. 4C. In this case, itis preferable to form the second electrode 14 using a highly reflectivematerial or to provide a reflective film above the second electrode 14.

In the light-emitting element 12, the layer 15 may have a stackedstructure so as to operate the light-emitting element 12 when voltage isapplied so that a potential of the second electrode 14 is higher thanthat of the first electrode 13, or the layer 15 may have a stackedstructure so as to operate the light-emitting element 12 when voltage isapplied so that a potential of the second electrode 14 is lower thanthat of the first electrode 13. In the former case, the transistor 11 isan n-channel transistor, and in the latter case, the transistor 11 is ap-channel transistor.

In this embodiment, an active-matrix light-emitting device in whichoperation of a light-emitting element is controlled by a transistor isdescribed. In addition, a passive-matrix light-emitting device in whicha light-emitting element is operated without provision of an element fordriving a transistor or the like on the substrate over which thelight-emitting element is formed may be manufactured.

Since any of the light-emitting elements described in the aboveembodiments is used in the light-emitting device described in Embodiment6, the light-emitting device can emit light of a color with high purity.In addition, the light-emitting device can have high emission efficiencyand consume a small amount of power.

Embodiment 7

In Embodiment 7, electronic devices each of which includes, as a partthereof, the light-emitting device described in Embodiment 6 isdescribed. The electronic device described in this embodiment has adisplay portion with high emission efficiency and reduced powerconsumption since the display portion includes the organometalliccomplex described in Embodiment 1. Further, the electric devicedescribed in this embodiment includes the display portion also withexcellent color reproducibility. In the case where the organometalliccomplex described in Embodiment 1 is used for a full-color display,various light-emitting substances can be used for a light-emittingelement of a color other than red and a light-emitting element having astructure similar to those described in Embodiments 2 to 5 can beemployed as the light-emitting element of a color other than red.

Electronic devices each including a light-emitting element manufacturedusing the organometallic complex of the present invention can be acamera such as a video camera or a digital camera, a goggle typedisplay, a navigation system, an audio reproducing device (car audiocomponent stereo, audio component stereo, or the like), a computer, agame machine, a portable information terminal (mobile computer, mobilephone, portable game machine, electronic book, or the like), and animage reproducing device provided with a recording medium (specifically,a device capable of reproducing a recording medium such as a digitalversatile disc (DVD) and provided with a display device that can displaythe image), and the like. Specific examples of these electronic devicesare illustrated in FIGS. 5A to 5E.

An example of a portable information terminal device 9200 is illustratedin FIG. 5A. The portable information terminal device 9200 incorporates acomputer and thus can process various types of data. An example of theportable information terminal device 9200 is a personal digitalassistant (PDA).

The portable information terminal device 9200 has a housing 9201 and ahousing 9203. The housing 9201 and the housing 9203 are joined to eachother with a joining portion 9207 so that the portable informationterminal device 9200 can be foldable. A display portion 9202 isincorporated in the housing 9201, and the housing 9203 is provided witha keyboard 9205. Needless to say, the structure of the portableinformation terminal device 9200 is not limited to the above, and may beprovided with an additional accessory as appropriate. In the displayportion 9202, light-emitting elements similar to those described in theabove embodiments are arranged in a matrix form. Features of thelight-emitting element include high emission efficiency and low powerconsumption. In addition, light emission of red with high luminousefficiency can be realized. The display portion 9202 including thelight-emitting element has a similar feature; therefore, in thisportable information terminal device, there is no deterioration of imagequality and low power consumption is achieved. With such features,deterioration compensating function circuits and power supply circuitscan be greatly reduced in number or in size in the portable informationterminal device. Therefore, the portable information terminal device canbe reduced in size and weight.

An example of a digital video camera 9500 is illustrated in FIG. 5B. Inthe digital video camera 9500, a display portion 9503 is incorporated ina housing 9501 and various operation portions are also provided. Notethat the structure of the digital video camera 9500 is not limited tothe above, and may be provided with an additional accessory asappropriate.

In this video camera, the display portion 9503 includes light-emittingelements similar to those described in the above embodiments, which arearranged in a matrix form. Features of the light-emitting elementinclude high emission efficiency and low power consumption. In addition,light emission of red with high luminous efficiency can be realized. Thedisplay portion 9503 including the light-emitting element has a similarfeature; therefore, in this digital video camera, there is nodeterioration of image quality and low power consumption is achieved.With such features, deterioration compensating function circuits andpower supply circuits can be greatly reduced in number or in size in thedigital video camera. Therefore, the digital video camera can be reducedin size and weight.

An example of a cellular phone 9100 is illustrated in FIG. 5C. Thecellular phone 9100 has a housing 9102 and a housing 9101. The housing9102 and the housing 9101 are joined with a joining portion 9103 so thatthe cellular phone is foldable. A display portion 9104 is incorporatedin the housing 9102, and operation keys 9106 are included in the housing9101. Note that the structure of the cellular phone 9100 is not limitedto the above, and may be provided with an additional accessory asappropriate.

In this cellular phone, the display portion 9104 includes light-emittingelements similar to those described in the above embodiments, which arearranged in a matrix form. Features of the light-emitting elementinclude high emission efficiency and low power consumption. In addition,light emission of red with high luminous efficiency can be realized. Thedisplay portion 9104 including the light-emitting element has a similarfeature; therefore, in this cellular phone, there is no deterioration ofimage quality and low power consumption is achieved. With such features,deterioration compensating function circuits and power supply circuitscan be greatly reduced in number or in size in a cellular phone.Therefore, the cellular phone can be reduced in size and weight. Inaddition, any of the light-emitting elements described in the aboveembodiments may also be used as a backlight of a display of a cellularphone or the like.

An example of a portable computer 9400 is illustrated in FIG. 5D. Thecomputer 9400 has a housing 9401 and a housing 9404, which are joined sothat the computer can be open and closed. A display portion 9402 isincorporated in the housing 9401, and the housing 9404 is provided witha keyboard 9403 and the like. Note that the structure of the computer9400 is not limited to the above, and may be provided with an additionalaccessory as appropriate.

In this computer, the display portion 9402 includes light-emittingelements similar to those described in the above embodiments, which arearranged in a matrix form. Features of the light-emitting elementinclude high emission efficiency and low power consumption. In addition,light emission of red with high luminous efficiency can be realized. Thedisplay portion 9402 including the light-emitting element has a similarfeature; therefore, in this computer, there is no deterioration of imagequality and low power consumption is achieved. With such features,deterioration compensating function circuits and power supply circuitscan be greatly reduced in number or in size in cellular phone.Therefore, the cellular phone can be reduced in size and weight.

An example of a television set 9600 is illustrated in FIG. 5E. In thetelevision set 9600, a display portion 9603 is incorporated in a housing9601. The display portion 9603 can display images. Here, the housing9601 is supported by a stand 9605.

The television set 9600 can be operated with an operation switch of thehousing 9601 or a separate remote controller 9610. Channels and volumecan be controlled with an operation key 9609 of the remote controller9610 so that an image displayed on the display portion 9603 can becontrolled. Furthermore, the remote controller 9610 may be provided witha display portion 9607 for displaying data output from the remotecontroller 9610.

Note that the television set 9600 is provided with a receiver, a modem,and the like. With the use of the receiver, general televisionbroadcasting can be received. Moreover, when the display device isconnected to a communication network with or without wires via themodem, one-way (from a sender to a receiver) or two-way (between asender and a receiver or between receivers) information communicationcan be performed.

In at least either the display portion 9607 or the display portion 9603of this television device, light-emitting elements similar to thosedescribed in the above embodiments are arranged in a matrix form.Features of the light-emitting element include high emission efficiencyand low power consumption. In addition, light emission of red with highluminous efficiency can be realized. The display portions including suchlight-emitting elements also have similar features.

From the above, the application range of the light-emitting devicedescribed in above embodiment is so wide that the light-emitting devicecan be applied to electronic devices of a variety of fields. With theuse of the organometallic complex described in Embodiment 1, electronicdevices which have display portions with low power consumption andexcellent color reproducibility can be provided.

The light-emitting device described in the above embodiment can also beused as a lighting device. An embodiment in which the light-emittingelement described in the above embodiments, is applied to as a lightingdevice is described with reference to FIG. 6.

Lighting devices such as a table lamp and a room light are illustratedin FIG. 6 as an application of the light-emitting device whose exampleis described in the above embodiment. The table lamp illustrated in FIG.6 includes a light source 3000. The light-emitting device, whose exampleis described in the above embodiment, is used as the light source 3000.Accordingly, a light-emitting device with low power consumption can beobtained. Since this light-emitting device can have a large area, thelighting device can be used as a light having a large area. In addition,since this light-emitting device is thin and consumes small amount ofpower, the light-emitting device can be used as a lighting device thatis thin and consumes small amount of power. Further, since thislight-emitting device can be flexible, for example, a light device canbe manufactured in a shape of a roll screen as a lighting device 3002.The television device illustrated in FIG. 5E may be placed in a roomwhere the light-emitting device described in this embodiment can beapplied to the indoor lighting devices 3001 and 3002 in this manner.

Example 1

In Example 1, a specific example of synthesis ofbis(2,3,5-triphenylpyrazinato)(2,2-dimethyl-3,5-hexanedionato)iridium(III) (abbr.: [Ir(tppr)₂(pac)]),which is an organometallic complex represented by Structural Formula(13) in Embodiment 1, is given.

First, 20 mL of 2-ethoxyethanol, 0.78 g of a binuclear complexdi-μ-chloro-bis[bis(2,3,5-triphenylpyrazinato)iridium(III)] (abbr.:[Ir(tppr)₂Cl]₂), 0.20 g of 2,2-dimethyl-3,5-hexanedion, and 0.49 g ofsodium carbonate were put in a recovery flask with a reflux pipe, andthe air in the flask was replaced with argon. Then, irradiation withmicrowaves (2.45 GHz, 100 W) for 30 minutes was performed to causereaction. Dichloromethane was added to the reacted solution andfiltration was carried out. The obtained filtrate was concentrated toprecipitate red powder. The powder was obtained by filtration and washedwith ethanol, and then, ether to obtain a red powdery solid, which wasan object, in a yield of 93%. Note that the irradiation with microwaveswas performed using a microwave synthesis system (Discover, manufacturedby CEM Corporation). The synthetic scheme of this step is represented by(E-1) below.

Nuclear magnetic resonance spectrometry (¹H-NMR) revealed that thecompound was [Ir(tppr)₂(pac)], which was an object. The obtainedanalysis result by ¹H-NMR is shown below and the ¹H-NMR chart is shownin FIG. 7.

¹H-NMR. δ (CDCl₃): 1.02 (s, 9H), 1.96 (s, 3H), 5.46 (s, 1H), 6.40 (d,1H), 6.48-6.57 (m, 3H), 6.65 (t, 2H), 6.91 (dt, 2H), 7.47-7.61 (m, 12H),7.82 (m, 4H), 8.08 (dt, 4H), 8.93 (d, 2H).

From these measurement results, it is known that in Example 1, theorganometallic complex represented by above Structural Formula (13),[Ir(tppr)₂(pac)], was obtained.

The sublimation temperature of the obtained organometallic complex,[Ir(tppr)₂(pac)], was measured with a high vacuum differential typedifferential thermal balance (TG-DTA2410SA, manufactured by Bruker AXSK.K.). The degree of vacuum was 2.5×10⁻³ Pa and the temperature increaserate was 10° C./min, and the temperature was increased. Under suchconditions, reduction in weight by 5% was observed at 226° C., which isindicative of a favorable sublimation property.

Next, an analysis of [Ir(tppr)₂(pac)] was conducted by anultraviolet-visible spectrometry. The ultraviolet spectrum was measuredwith an ultraviolet-visible spectrophotometer (V-550, manufactured byJASCO Corporation), using a dichloromethane solution (0.057 mmol/L) atroom temperature. Further, the emission spectrum of [Ir(tppr)₂(pac)] wasmeasured with a fluorescence spectrophotometer (FS920, manufactured byHamamatsu Photonics K.K.), using a degassed dichloromethane solution(0.34 mmol/L) at room temperature. A measurement result is shown in FIG.8 in which the horizontal axis indicates a wavelength (nm) and thevertical axes indicate an absorption intensity (arbitrary unit) and anemission intensity (arbitrary unit).

As is shown in FIG. 8, an organometallic complex [Ir(tppr)₂(pac)] has alight emission peak at 622 nm and red light emission was observed fromthe dichloromethane solution.

Example 2

In Example 2, a specific example of synthesis ofbis(2,3,5-triphenylpyrazinato)(2,6-dimethyl-3,5-heptanedionato)iridium(III) (abbr.:[Ir(tppr)₂(dibm)]), which is an organometallic complex represented byStructural Formula (15) in Embodiment 1, is given.

First, 20 mL of 2-ethoxyethanol, 0.65 g of a binuclear complexdi-μ-chloro-bis[bis(2,3,5-triphenylpyrazinato)iridium(III)] (abbr.:[Ir(tppr)₂Cl]₂), 0.18 g of 2,6-dimethyl-3,5-heptanedione, and 0.41 g ofsodium carbonate were put in a recovery flask with a reflux pipe, andthe air in the flask was replaced with argon. Then, irradiation withmicrowaves (2.45 GHz, 100 W) for 30 minutes was performed to causereaction. Dichloromethane was added to the reacted solution andfiltration was carried out. The obtained filtrate was concentrated toprecipitate red powder. The powder was obtained by filtration and washedwith ethanol, and then, ether to obtain a red powdery solid, which wasan object, in a yield of 92%. Note that the irradiation with microwaveswas performed using a microwave synthesis system (Discover, manufacturedby CEM Corporation). The synthetic scheme of this step is represented by(E-2) below.

Nuclear magnetic resonance spectrometry (¹H-NMR) revealed that thecompound was [Ir(tppr)₂(dibm)], which was an object. An analysis resultby ¹H-NMR is shown below and the ¹H-NMR chart is shown in FIG. 9.

¹H-NMR. δ (CDCl₃): 0.88 (d, 6H), 1.05 (d, 6H), 2.36 (sep, 2H), 5.30 (s,1H), 6.51 (t, 4H), 6.64 (dt, 2H), 6.92 (d, 2H), 7.45-7.56 (m, 12H), 7.81(brm, 4H), 8.07 (dd, 4H), 8.87 (s, 2H).

From these measurement results, it is known that in Example 2, theorganometallic complex represented by above Structural Formula (15),[Ir(tppr)₂(dibm)], was obtained.

The sublimation temperature of the obtained organometallic complex,[Ir(tppr)₂(dibm)], was measured with a high vacuum differential typedifferential thermal balance (TG-DTA2410SA, manufactured by Bruker AXSK.K.). The degree of vacuum was 2.5×10⁻³ Pa and the temperature increaserate was 10° C./min, and the temperature was increased. Under suchconditions, reduction in weight by 5% was observed at 230° C., which isindicative of a favorable sublimation property.

Next, an analysis of [Ir(tppr)₂(dibm)] was conducted by anultraviolet-visible spectrometry. The ultraviolet spectrum was measuredwith an ultraviolet-visible spectrophotometer (V-550, manufactured byJASCO Corporation), using a dichloromethane solution (0.056 mmol/L) atroom temperature. Further, the emission spectrum of [Ir(tppr)₂(dibm)]was measured with a fluorescence spectrophotometer (FS920, manufacturedby Hamamatsu Photonics K.K.), using a degassed dichloromethane solution(0.33 mmol/L) at room temperature. A measurement result is shown in FIG.10 in which the horizontal axis indicates a wavelength (nm) and thevertical axes indicate an absorption intensity (arbitrary unit) and anemission intensity (arbitrary unit).

As is shown in FIG. 10, an organometallic complex [Ir(tppr)₂(dibm)] hasa light emission peak at 620 nm and red light emission was observed fromthe dichloromethane solution.

Example 3

In Example 3, a specific example of synthesis ofbis(2,3,5-triphenylpyrazinato) (dipivaloylmethanato)iridium(III) (abbr.:[Ir(tppr)₂(dpm)]), which is an organometallic complex represented byStructural Formula (12) in Embodiment 1, is given.

First, 25 mL of 2-ethoxyethanol, 0.40 g of a binuclear complex[Ir(tppr)₂Cl]₂, 0.14 ml of dipivaloylmethane, and 0.25 g of sodiumcarbonate were put in a recovery flask with a reflux pipe, and the airin the flask was replaced with argon. Then, irradiation with microwaves(2.45 GHz, 150 W) for 15 minutes was performed to cause reaction. Thereacted solution was filtered and the obtained filtrate wasrecrystallized with ethanol to precipitate red powder. The obtainedpowder was washed with ethanol, and then, diethylether to obtain a redpowdery solid, which was an object, in a yield of 75%. Note that theirradiation with microwaves was performed using a microwave synthesissystem (Discover, manufactured by CEM Corporation). The synthetic schemeof this step is represented by (E-3) below.

Nuclear magnetic resonance spectrometry (¹H-NMR) revealed that thecompound was [Ir(tppr)₂(dpm)], which was an object. An analysis resultby ¹H-NMR is shown below and the ¹H-NMR chart is shown in FIG. 11.

¹H-NMR. δ (CDCl₃): 1.02 (s, 18H), 5.64 (s, 1H), 6.51 (m, 4H), 6.64 (m,2H), 6.92 (d, 2H), 7.44-7.56 (m, 12H), 7.80 (brs, 4H), 8.06 (d, 4H),8.86 (s, 2H).

From these measurement results, it is known that in Example 3, theorganometallic complex represented by above Structural Formula (12),[Ir(tppr)₂(dpm)], was obtained.

The sublimation temperature of the obtained organometallic complex,[Ir(tppr)₂(dpm)], was measured with a high vacuum differential typedifferential thermal balance (TG-DTA2410SA, manufactured by Bruker AXSK.K.). The degree of vacuum was 2.5×10⁻³ Pa and the temperature increaserate was 10° C./min, and the temperature was increased. Under suchconditions, reduction in weight by 5% was observed at 220° C., which isindicative of a favorable sublimation property.

Next, an analysis of [Ir(tppr)₂(dpm)] was conducted by anultraviolet-visible spectrometry. The ultraviolet spectrum was measuredwith an ultraviolet-visible spectrophotometer (V-550, manufactured byJASCO Corporation), using a dichloromethane solution (0.094 mmol/L) atroom temperature. Further, the emission spectrum of [Ir(tppr)₂(dpm)] wasmeasured with a fluorescence spectrophotometer (FS920, manufactured byHamamatsu Photonics K.K.), using a degassed dichloromethane solution(0.33 mmol/L) at room temperature. The excitation wavelength was 465 nm.A measurement result is shown in FIG. 12 in which the horizontal axisindicates a wavelength (nm) and the vertical axes indicate an absorptionintensity (arbitrary unit) and an emission intensity (arbitrary unit).

As is shown in FIG. 12, an organometallic complex [Ir(tppr)₂(dpm)] has alight emission peak at 630 nm and red light emission was observed fromthe dichloromethane solution.

Example 4

In Example 4, a light-emitting element according to one embodiment ofthe present invention is described with reference to FIG. 13. A chemicalformula of the material used in this example and Example 5 are shownbelow.

A manufacturing method of light-emitting elements 1 to 3 of this exampleand a comparative light-emitting element 1 is described below.

First, the light-emitting element 1 is described. Indium tin oxidecontaining silicon oxide was deposited over a glass substrate 2101 bysputtering to form a first electrode 2102 with a thickness of 110 nm andan electrode area of 2 mm×2 mm.

Then, the substrate provided with the first electrode was fixed on asubstrate holder which was provided in a vacuum evaporation apparatus,in such a manner that a surface provided with the first electrode faceddownward. After that, the pressure in the vacuum evaporation apparatuswas reduced to approximately 10⁻⁴ Pa. Then, a layer 2103 including acomposite material of an organic compound and an inorganic compound wasformed on the first electrode 2102 by co-evaporation of NPB andmolybdenum(VI) oxide. The thickness of the layer 2103 was 50 nm, and theweight ratio of NPB to molybdenum(VI) oxide was 4:1 (=NPB:molybdenumoxide). Note that the co-evaporation method refers to an evaporationmethod in which evaporation is carried out from a plurality ofevaporation sources at the same time in one treatment chamber.

Then, a film of 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbr.:NPB) was formed to a thickness of 10 nm over the layer 2103 includingthe composite material by the evaporation method using resistanceheating to form a hole-transporting layer 2104.

In addition, bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(abbr.: BAlq), NPB, andbis(2,3,5-triphenylpyrazinato)(2,2-dimethyl-3,5-hexanedionato)iridium(III)(abbr.: [Ir(tppr)₂(pac)]) represented by Structural Formula (13) wereco-evaporated to form the light-emitting layer 2105 having a thicknessof 50 nm over the hole-transporting layer 2104. Here, the weight ratioof BAlq, NPB, and [Ir(tppr)₂(pac)] was adjusted to 1:0.1:0.06(=BAlq:NPB:[Ir(tppr)₂(pac)]).

Then, tris(8-quinolinolato)aluminum(III) (abbr.: Alq) was deposited overthe light-emitting layer 2105 to a thickness of 10 nm, andbathophenanthroline (abbr.: BPhen) was deposited thereover to athickness of 20 nm by an evaporation method using resistance heating toform an electron-transporting layer 2106.

Further, an electron-injecting layer 2107 was formed on theelectron-transporting layer 2106 by evaporating lithium fluoride to athickness of 1 nm.

Lastly, by forming a film of aluminum with a film thickness of 200 nmover the electron-injecting layer 2107 by the evaporation method usingresistance heating, a second electrode 2108 was formed. Thus, thelight-emitting element 1 was manufactured.

Next, the light-emitting element 2 is described. The light-emittingelement 2 was manufactured in a manner similar to that of thelight-emitting element 1 except for the light-emitting layer 2105. Asfor the light-emitting element 2, BAlq, NPB, andbis(2,3,5-triphenylpyrazinato)(2,6-dimethyl-3,5-heptanedionato)iridium(III)(abbr.: [Ir(tppr)₂(dipm)]) represented by Structural Formula (15) wereco-evaporated to form the light-emitting layer 2105 having a thicknessof 50 nm over the hole-transporting layer 2104. Here, the weight ratioof BAlq, NPB, and [Ir(tppr)₂(dipm)] was adjusted to 1:0.1:0.06(=BAlq:NPB:[Ir(tppr)₂(dipm)]). Thus, the light-emitting element 2 ofthis example was obtained.

Next, the light-emitting element 3 is described. The light-emittingelement 3 was manufactured in a manner similar to that of thelight-emitting element 1 except for the light-emitting layer 2105. Asfor the light-emitting element 3, BAlq, NPB, andbis(2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III) (abbr.:[Ir(tppr)₂(dpm)]) represented by Structural Formula (12) wereco-evaporated to form the light-emitting layer 2105 having a thicknessof 50 nm over the hole-transporting layer 2104. Here, the weight ratioof BAlq, NPB, and [Ir(tppr)₂(dpm)] was adjusted to 1:0.1:0.06(=BAlq:NPB:[Ir(tppr)₂(dpm)]). Thus, the light-emitting element 3 of thisexample was obtained.

Next, the comparative light-emitting element 1 is described. Thecomparative light-emitting element 1 was manufactured in a mannersimilar to that of the light-emitting element 1 except for thelight-emitting layer 2105. As for the comparative light-emitting element1, BAlq, NPB, and(acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium(III) (abbr.:[Ir(tppr)₂(acac)]) represented by Structural Formula (50) wereco-evaporated to form the light-emitting layer 2105 having a thicknessof 50 nm over the hole-transporting layer 2104. Here, the weight ratioof BAlq, NPB, and [Ir(tppr)₂(acac)] was adjusted to 1:0.1:0.06(=BAlq:NPB:[Ir(tppr)₂(acac)]). Thus, the comparative light-emittingelement 1 of this example was obtained.

The thus obtained light-emitting elements 1 to 3 and the comparativelight-emitting element 1 were put into a glove box under a nitrogenatmosphere so that each of the light-emitting elements was sealed so asnot to be exposed to the air. Then, the operation characteristics ofthese light-emitting elements were measured. The measurement was carriedout at room temperature (under an atmosphere maintaining 25° C.).

Current density-luminance characteristics of the light-emitting elements1 to 3 and the comparative light-emitting element 1 are shown in FIG.14. In FIG. 14, the horizontal axis represents current density (mA/cm²)and the vertical axis represents luminance (cd/m²). In addition,voltage-luminance characteristics thereof are shown in FIG. 15. In FIG.15, the horizontal axis represents applied voltage (V) and the verticalaxis represents luminance (cd/m²).

Further, emission spectra of the light-emitting elements 1 to 3 and thecomparative light-emitting element 1 at a current of 0.5 mA are shown inFIGS. 16A and 16B. Note that FIG. 16B shows enlarged parts of theemission spectra in the range of 610 nm to 640 nm in FIG. 16A. From FIG.16, the emission peak of the light-emitting elements 1 and 3 is 622 nm,the emission peak of the light-emitting element 3 is 624 nm, and theemission peak of the comparative light-emitting element 1 is 619 nm. Inaddition, a CIE chromaticity coordinate of the light-emitting element 1at a luminance of 970 cd/m² was (x=0.67, y=0.33). A CIE chromaticitycoordinate of the light-emitting element 2 at a luminance of 1100 cd/m²was (x=0.67, y=0.33). A CIE chromaticity coordinate of thelight-emitting element 3 at a luminance of 940 cd/m² was (x=0.67,y=0.33). A CIE chromaticity coordinate of the comparative light-emittingelement 1 at a luminance of 1070 cd/m² was (x=0.66, y=0.34).Accordingly, while any of the manufactured light-emitting elements 1 to3 and the comparative light-emitting element 1 exhibited red lightemission, the light-emitting elements 1 to 3 exhibited more favorablered light emission than the comparative light-emitting element 1.

Further, as for the light-emitting element 1, when the luminance was 970cd/m², the voltage was 7.2 V and the external quantum efficiency was20%. As for the light-emitting element 2, when the luminance was 1100cd/m², the voltage was 6.8 V and the external quantum efficiency was22%. As for the light-emitting element 3, when the luminance was 940cd/m², the voltage was 6.6 V and the external quantum efficiency was21%. As for the comparative light-emitting element 1, when the luminancewas 1070 cd/m², the voltage was 7.2 V and the external quantumefficiency was 21%.

Further, reliability tests of the light-emitting element 1, thelight-emitting element 2, the light-emitting element 3, and thecomparative light-emitting element 1 which were formed were carried out.In the reliability tests, the initial luminance was set at 1000 cd/m²,these elements were operated at constant current density, and theluminance was measured at regular intervals. Results of the reliabilitytests are shown in FIG. 21. In FIG. 21, the horizontal axis representscurrent flow time (hour) and the vertical axis represents the proportionof luminance with respect to the initial luminance at each time, thatis, normalized luminance (%).

As shown in FIG. 21, the light-emitting element 1, the light-emittingelement 2, the light-emitting element 3, and the comparativelight-emitting element 1 are light-emitting elements whose luminance ishardly reduced with time, and which have a long lifetime. Thelight-emitting elements 1 to 3 kept 82%, 80%, and 87% of the initialluminance, respectively, after 7000-hour-operation. The luminance of thecomparative light-emitting element 1 after 7000-hour-operation was 78%of the initial luminance. Therefore, reduction in the luminance overtime of the light-emitting elements 1 to 3 is less likely to occur thanthat of the comparative light-emitting element 1 and the light-emittingelements 1 to 3 have a long lifetime.

Accordingly, it was confirmed that each of the light-emitting elements 1to 3 of this example had sufficient characteristics to serve as alight-emitting element. In addition, the light-emitting elements 1 to 3exhibited favorable red light emission and had a long lifetime. Further,it was confirmed that the light-emitting element 2 using[Ir(tppr)₂(dibm)], an organometallic complex in which both R²¹ and R²²are isopropyl groups each having 3 carbon atoms represented by GeneralFormula (G1), and the light-emitting element 3 using [Ir(tppr)₂(dpm)],an organometallic complex in which both R²¹ and R²² are tert-butylgroups each having 4 carbon atoms represented by General Formula (G1)are light-emitting elements capable of being operated at a low voltage.

In FIG. 25, sublimation properties of [Ir(tppr)₂(dpm)], anorganometallic complex used for the light-emitting element 3, and[Ir(tppr)₂(acac)], an organometallic complex used for the comparativelight-emitting element 1, are shown. The sublimation temperatures weremeasured with a high vacuum differential type differential thermalbalance (TG-DTA2410SA, manufactured by Bruker AXS K.K.) under thecondition that the degree of vacuum was 2.5×10⁻³ Pa and the temperatureincrease rate was 10° C./min.

As shown in FIG. 25, [Ir(tppr)₂(dpm)], the organometallic complex usedfor the light-emitting element 3, is likely to sublime at a lowertemperature than [Ir(tppr)₂(acac)], the organometallic complex used forthe comparative light-emitting element 1, and has a favorablesublimation property. Thus, [Ir(tppr)₂(dpm)], the organometalliccomplex, can sublime without pyrolysis, and in a case where alight-emitting layer including a low molecular compound is formed by anevaporation method, it can be avoided that decomposed matters are mixedin the light-emitting layer. Accordingly, the light-emitting element 3according to this embodiment, which used the organometallic compound,can be a light-emitting element with a long lifetime.

Example 5

In Example 5, a light-emitting element according to one embodiment ofthe present invention is described with reference to FIG. 17.

A manufacturing method of the light-emitting element 4 and thecomparative light-emitting element 2 of this example is described below.

First, the light-emitting element 4 is described. Indium tin oxidecontaining silicon oxide was deposited over a glass substrate 2101 bysputtering to form a first electrode 2102 with a thickness of 110 nm andan electrode area of 2 mm×2 mm.

Then, the substrate provided with the first electrode was fixed on asubstrate holder which was provided in a vacuum evaporation apparatus,in such a manner that a surface provided with the first electrode faceddownward. After that, the pressure in the vacuum evaporation apparatuswas reduced to approximately 10⁻⁴ Pa. Then, a layer 2103 including acomposite material of an organic compound and an inorganic compound wasformed on the first electrode 2102 by co-evaporation of NPB andmolybdenum(VI) oxide. The thickness of the layer 2103 was 50 nm, and theweight ratio of NPB to molybdenum(VI) oxide was 4:1 (=NPB:molybdenumoxide). Note that the co-evaporation method refers to an evaporationmethod in which evaporation is carried out from a plurality ofevaporation sources at the same time in one treatment chamber.

Then, a film of 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbr.:NPB) was formed to a thickness of 10 nm over the layer 2103 includingthe composite material by the evaporation method using resistanceheating to form a hole-transporting layer 2104.

In addition, bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(abbr.: BAlq), NPB, andbis(2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III) (abbr.:[Ir(tppr)₂(dpm)]) represented by Structural Formula (12) wereco-evaporated to form a first light-emitting layer 2105 a having athickness of 20 nm over the hole-transporting layer 2104. Here, theweight ratio of BAlq, NPB, and [Ir(tppr)₂(dpm)] was adjusted to1:0.25:0.06 (=BAlq:NPB:[Ir(tppr)₂(dpm)]).

Then, as in the formation of the first light-emitting layer 2105 a,BAlq, NPB, and [Ir(tppr)₂(dpm)] represented by Structural Formula (12)were co-evaporated to form a second light-emitting layer 2105 b having athickness of 30 nm over the first light-emitting layer 2105 a. Here, theweight ratio of BAlq, NPB, and [Ir(tppr)₂(dpm)] was adjusted to1:0.1:0.06 (=BAlq:NPB:[Ir(tppr)₂(dpm)]).

Then, tris(8-quinolinolato)aluminum (abbr.: Alq₃) was deposited over thesecond light-emitting layer 2105 b to a thickness of 10 nm, andbathophenanthroline (abbr.: BPhen) was deposited thereover to athickness of 20 nm by an evaporation method using resistance heating toform an electron-transporting layer 2106.

Further, an electron-injecting layer 2107 was formed on theelectron-transporting layer 2106 by evaporating lithium fluoride to athickness of 1 nm.

Lastly, by forming a film of aluminum with a film thickness of 200 nmover the electron-injecting layer 2107 by the evaporation method usingresistance heating, a second electrode 2108 was formed. Thus, thelight-emitting element 4 was manufactured.

Next, the comparative light-emitting element 2 is described. Thecomparative light-emitting element 2 was manufactured in a mannersimilar to that of the light-emitting element 4 except for the firstlight-emitting layer 2105 a and the second light-emitting layer 2105 b.As for the comparative light-emitting element 2, BAlq, NPB, and(acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium(III) (abbr.:[Ir(tppr)₂(acac)]) represented by Structural Formula (50) wereco-evaporated to form the first light-emitting layer 2105 a having athickness of 20 nm over the hole-transporting layer 2104. Here, theweight ratio of BAlq, NPB, and [Ir(tppr)₂(acac)] was adjusted to1:0.25:0.06 (=BAlq:NPB:[Ir(tppr)₂(acac)]).

Then, BAlq, NPB, and [Ir(tppr)₂(acac)] were co-evaporated to form thesecond light-emitting layer 2105 b having a thickness of 30 nm over thefirst light-emitting layer 2105 a. Here, the weight ratio of BAlq, NPB,and [Ir(tppr)₂(acac)] was adjusted to 1:0.1:0.06(=BAlq:NPB:[Ir(tppr)₂(acac)]). Thus, the comparative light-emittingelement 2 of this example was obtained.

The thus obtained light-emitting element 4 and the comparativelight-emitting element 2 were put into a glove box under a nitrogenatmosphere so that each of the light-emitting elements was sealed so asnot to be exposed to the air. Then, the operation characteristics ofthese light-emitting elements were measured. The measurement was carriedout at room temperature (under an atmosphere maintaining 25° C.).

Current density-luminance characteristics of the light-emitting element4 and the comparative light-emitting element 2 are shown in FIG. 18. InFIG. 18, the horizontal axis represents current density (mA/cm²) and thevertical axis represents luminance (cd/m²). In addition,voltage-luminance characteristics thereof are shown in FIG. 19. In FIG.19, the horizontal axis represents applied voltage (V) and the verticalaxis represents luminance (cd/m²). From FIG. 19, the light-emittingelement 4 can be operated at a lower voltage than the comparativelight-emitting element 2.

Further, emission spectra of the light-emitting element 4 and thecomparative light-emitting element 2 at a current of 0.5 mA are shown inFIG. 20. From FIG. 20, the emission peak of the light-emitting element 4is 624 nm, the emission peak of the comparative light-emitting element 2is 619 nm. In addition, a CM chromaticity coordinate of thelight-emitting element 4 at a luminance of 970 cd/m² was (x=0.66,y=0.34). A CIE chromaticity coordinate of the comparative light-emittingelement 2 at a luminance of 900 cd/m² was (x=0.65, y=0.35). Accordingly,while any of the manufactured light-emitting element 4 and thecomparative light-emitting element 2 exhibited red light emission, thelight-emitting element 4 exhibited more favorable red light emissionthan the comparative light-emitting element 2.

Further, as for the light-emitting element 4, when the luminance was 970cd/m², the voltage was 7.0 V and the external quantum efficiency was22%. As for the comparative light-emitting element 2, when the luminancewas 900 cd/m², the voltage was 7.8 V and the external quantum efficiencywas 21%.

Further, reliability tests of the light-emitting element 4 and thecomparative light-emitting element 2 which were formed were carried out.In the reliability tests, the initial luminance was set at 1000 cd/m²,these elements were operated at the constant current density, and theluminance was measured at regular intervals. Results of the reliabilitytests are shown in FIG. 22. In FIG. 22, the horizontal axis representscurrent flow time (hour) and the vertical axis represents the proportionof luminance with respect to the initial luminance at each time, thatis, normalized luminance (%).

As shown in FIG. 22, the light-emitting element 4 and the comparativelight-emitting element 2 are light-emitting elements whose luminancesare hardly reduced with time, and has a long lifetime. Thelight-emitting element 4 kept 94% of the initial luminance after1100-hour-operation. The luminance of the comparative light-emittingelement 2 after 1100-hour-operation was 93% of the initial luminance.Therefore, decline in the luminance over time of the light-emittingelement 4 is less likely to occur than that of the comparativelight-emitting element 2 and the light-emitting element 4 has a longlifetime.

Accordingly, it was confirmed that the light-emitting element 4 of thisexample has sufficient characteristics to serve as a light-emittingelement. In addition, the light-emitting element 4 exhibited favorablered light emission and had a long lifetime. Further, it was confirmedthat the light-emitting element 4 using [Ir(tppr)₂(acac)], anorganometallic complex in which both R²¹ and R²² are tert-butyl groupseach having 4 carbon atoms represented by General Formula (G1) is alight-emitting element capable of being operated at a lower voltage thanthe comparative light-emitting element 2 using [Ir(tppr)₂(acac)], anorganometallic complex in which both R²¹ and R²² are methyl groups eachhaving 1 carbon atom represented by General Formula (G1).

Example 6

In this example, a specific example of synthesis ofbis(5-phenyl-2,3-di-m-tolylpyrazinato)(dipivaloylmethanato)iridium(III)(abbr.: [Ir(5dmtppr)₂(dpm)]), which is an organometallic complexrepresented by following Structural Formula (45), according to anembodiment of the present invention, is described. The organometalliccomplex [Ir(5dmtppr)₂(dpm)] represented by Structural Formula (45) has astructure represented by General Formula (G1) in Embodiment 1, in whichR¹, R², R⁴ to R⁷, and R⁹ to R¹⁵ are hydrogen, R³ and R⁸ are methylgroups each having 1 carbon atom, and R²¹ and R²² are tert-butyl groupseach having 4 carbon atoms.

Note that the irradiation with microwaves was performed using amicrowave synthesis system (Discover, manufactured by CEM Corporation)in this example described below.

<Step 1: Synthesis of 2,3-di-m-tolylpyrazine>

First, 2.39 g of 2,3-dichloropyrazine, 4.51 g of 3-methylphenyl boronicacid, 3.74 g of sodium carbonate, 0.17 g ofbis(triphenylphosphine)palladium(II)dichloride (abbr.: Pd(PPh₃)₂Cl₂), 15mL of water, and 15 mL of acetonitrile were put in a round-bottomedflask with a reflux pipe, and the air in the flask was replaced withargon. This reaction container was subjected to irradiation withmicrowaves (2.45 GHz, 100 W) for 3 hours and 40 minutes to be heated.Then, water was added to this solution and an organic layer wasextracted with dichloromethane. The obtained organic layer was washedwith water and dried with magnesium sulfate. After the drying, thesolution was filtrated. The solvent of this solution was distilled offto obtain 2,3-di-m-tolylpyradine (a white powder, yield: 80%). Asynthetic scheme of Step 1 is represented by (E4-1) below.

<Step 2: Synthesis of 2,3-di-m-tolylpyrazine-1-oxide>

In a nitrogen atmosphere, 3.32 g of 2,3-di-m-tolylpyradine that wasobtained by Step 1 above was dissolved in 50 mL of dichloromethane, 4.42g of 3-chlorobenzoic acid (abbr.: mCPBA) was added, and the solution wasstirred for 24 hours at room temperature. Then, water was added to thissolution and an organic layer was extracted with dichloromethane. Theobtained organic layer was washed with a saturated sodiumhydrogencarbonate water solution and dried with magnesium sulfate. Afterthe drying, the solution was filtrated. The solvent of this solution wasdistilled off and purification was conducted by silica gel columnchromatography which uses ethyl acetate as a developing solvent.Further, recrystallization was caused with a mixed solvent ofdichloromethane and hexane to obtain 2,3-di-m-tolylpyrazine-1-oxide (awhite powder, yield: 59%). A synthesis scheme of Step 2 is representedby (E4-2) below.

<Step 3: Synthesis of 5-chloro-2,3-di-m-tolylpyrazine>

In a nitrogen atmosphere, to 2.08 g of 2,3-di-m-tolylpyradine-1-oxidethat was obtained by Step 2 above, 12 mL of phosphoryl chloride wasadded and reflux for 1 hour was performed by heating. Then, thissolution was added to ice water. Potassium carbonate was added to thisaqueous solution to adjust the aqueous solution so that it is neutral,and an organic layer was extracted with dichloromethane. The obtainedorganic layer was washed with water and dried with magnesium sulfate.After the drying, the solution was filtrated. The solvent of thissolution was distilled off to obtain 5-chloro-2,3-di-m-tolylpyrazine (ayellow oily substance, yield: 100%). A synthesis scheme of Step 3 isrepresented by (E4-3) below.

Step 4: Synthesis of 5-phenyl-2,3-di-m-tolylpyrazine (abbr.: H5dmtppr)>

2.36 g of 5-chloro-2,3-di-m-tolylpyrazine that was obtained by Step 3above, 0.98 g of phenylboronic acid, 0.85 g of sodium carbonate, 0.036 gof bis(triphenylphosphine)palladium(II)dichloride (abbr.: Pd(PPh₃)₂Cl₂),15 mL of water, and 15 mL of acetonitrile were put in a recovery flaskwith a reflux pipe, and the air in the flask was replaced with argon.This reaction container was subjected to irradiation with microwaves(2.45 GHz, 100 W) for 1 hour and 30 minutes to be heated. Then, waterwas added to this solution and an organic layer was extracted withdichloromethane. The obtained organic layer was washed with water anddried with magnesium sulfate. After the drying, the solution wasfiltrated. The solvent of this solution was distilled off to obtainH5dmtppr (an orange oily substance, yield: 100%). A synthesis scheme ofStep 4 is represented by (E4-4) below.

<Step 5: Synthesis ofdi-μ-chloro-bis[bis(5-phenyl-2,3-di-m-tolylpyrazinato)iridium(III)](abbr.: [Ir(5dmtppr)₂Cl]₂)>

Then, 15 mL of 2-ethoxyethanol, 5 mL of water, 2.84 g of5-phenyl-2,3-di-m-tolylpyrazine that was obtained by Step 4 above, 1.01g of iridium chloride hydrate (IrCl₃.nH₂O) (manufactured by Furuya MetalCo., Ltd.) were put in a recovery flask with a reflux pipe, and theatmosphere in the flask was substituted by argon. Then, irradiation withmicrowaves (2.45 GHz, 100 W) for 30 minutes was performed to causereaction. The reacted solution was concentrated and the obtained residuewas washed with ethanol to obtain a binuclear complex [Ir(5dmtppr)₂Cl]₂(a red powder, yield: 88%). A synthetic scheme of Step 5 is representedby (E4-5) below.

<Step 6: Synthesis ofbis(5-phenyl-2,3-di-m-tolylpyrazinato)(dipivaloylmethanato)iridium(III)(abbr.: [Ir(5dmtppr)₂(dpm)]>

First, 25 mL of 2-ethoxyethanol, 2.66 g of [Ir(5dmtppr)₂Cl]₂, which is abinuclear complex obtained in Step 2 above, 0.91 mL ofdipivaloylmethane, and 1.57 g of sodium carbonate were put in a recoveryflask with a reflux pipe, and the air in the flask was replaced withargon. Then, irradiation with microwaves (2.45 GHz, 100 W) for 30minutes was performed to cause reaction. The reacted solution wasfiltered and the obtained solvent of the filtrate was distilled off andpurification was conducted by silica gel column chromatography whichuses toluene as a developing solvent. Further, recrystallization wascaused with methanol to obtain a dark red powder in a yield of 77%,which was an object. A synthetic scheme of Step 6 is represented by(E4-6) below.

Note that the dark red power obtained by Step 6 above was confirmed tobe an object [Ir(5dmtppr)₂(dpm)] by nuclear magnetic resonancespectrometry (¹H-NMR). The ¹H-NMR analysis result of the obtainedsubstance is shown below. A ¹H-NMR chart is shown in FIG. 23.

¹H-NMR. δ (CDCl₃): 1.02 (m, 18H), 1.88 (s, 6H), 2.46 (s, 6H), 5.16 (s,1H), 6.36 (d, 2H), 6.48 (dd, 2H), 6.67 (s, 2H), 7.60-7.35 (m, 14H), 8.06(m, 4H), 8.85 (s, 2H).

From these measurement results, it is understood that in this example,[Ir(5dmtppr)₂(dpm)], the organometallic complex represented by aboveStructural Formula (45) was obtained.

Next, [Ir(5dmtppr)₂(dpm)] was analyzed by ultraviolet-visible (UV)absorption spectroscopy. The UV spectrum was measured with anultraviolet-visible spectrophotometer (V-550, manufactured by JASCOCorporation), using a dichloromethane solution (0.091 mmol/L) at roomtemperature. Further, an emission spectrum of [Ir(5dmtppr)₂(dpm)] wasmeasured. The emission spectrum was measured with use of a fluorescencespectrophotometer (FS920, manufactured by Hamamatsu Photonics K.K.),using a degassed dichloromethane solution (0.55 mmol/L) at roomtemperature. The measurement results are shown in FIG. 24. Thehorizontal axis indicates a wavelength (nm) and the vertical axesindicate an absorption intensity (arbitrary unit) and an emissionintensity (arbitrary unit).

As shown in FIG. 24, [Ir(5dmtppr)₂(dpm)], the organometallic complexaccording to an embodiment of the present invention, has a peak ofemission spectrum at 639 nm, and red light was observed from thedichloromethane solution.

This application is based on Japanese Patent Application serial No.2008-293731 filed with Japan Patent Office on Nov. 17, 2008, the entirecontents of which are hereby incorporated by reference.

1. A light-emitting element comprising: a pair of electrodes; and alayer including a host material and a guest material, interposed betweenthe pair of electrodes, wherein the host material includes a lowmolecular compound, wherein the guest material includes anorganometallic complex represented by General Formula (G1),

wherein each of R¹ to R¹⁵ represents hydrogen or an alkyl group having 1to 4 carbon atoms, wherein one of R²¹ and R²² represents an alkyl grouphaving 2 to 10 carbon atoms and the other of R²¹ and R²² represents analkyl group having 1 to 10 carbon atoms, wherein M is a central metaland represents an element belonging to Group 9 or Group 10, and whereinn is 1 or
 2. 2. The light-emitting element according to claim 1, whereinn is 2 when the central metal represents the element belonging to Group9.
 3. The light-emitting element according to claim 1, wherein n is 1when the central metal represents the element belonging to Group
 10. 4.The light-emitting element according to claim 1, wherein the centralmetal is iridium or platinum.
 5. The light-emitting element according toclaim 1, wherein the layer is a light-emitting layer.
 6. Thelight-emitting element according to claim 1, wherein a molecular weightof the low molecular compound is greater than or equal to 100 and lessthan or equal to
 150. 7. A light-emitting element comprising: a pair ofelectrodes; and a layer including a host material and a guest material,interposed between the pair of electrodes, wherein the host materialincludes a low molecular compound, wherein the guest material includesan organometallic complex represented by General Formula (G2),

wherein one of R²¹ and R²² represents an alkyl group having 2 to 10carbon atoms and the other of R²¹ and R²² represents an alkyl grouphaving 1 to 10 carbon atoms, wherein M is a central metal and representsan element belonging to Group 9 or Group 10, and wherein n is 1 or
 2. 8.The light-emitting element according to claim 7, wherein n is 2 when thecentral metal represents the element belonging to Group
 9. 9. Thelight-emitting element according to claim 7, wherein n is 1 when thecentral metal represents the element belonging to Group
 10. 10. Thelight-emitting element according to claim 7, wherein the central metalis iridium or platinum.
 11. The light-emitting element according toclaim 7, wherein the layer is a light-emitting layer.
 12. Thelight-emitting element according to claim 7, wherein a molecular weightof the low molecular compound is greater than or equal to 100 and lessthan or equal to
 150. 13. A light-emitting device comprising alight-emitting element, the light-emitting element comprising: a pair ofelectrodes; and a layer including a host material and a guest material,interposed between the pair of electrodes, wherein the host materialincludes a low molecular compound, wherein the guest material includesan organometallic complex represented by General Formula (G1),

wherein each of R¹ to R¹⁵ represents hydrogen or an alkyl group having 1to 4 carbon atoms, wherein one of R²¹ and R²² represents an alkyl grouphaving 2 to 10 carbon atoms and the other of R²¹ and R²² represents analkyl group having 1 to 10 carbon atoms, wherein M is a central metaland represents an element belonging to Group 9 or Group 10, and whereinn is 1 or
 2. 14. The light-emitting device according to claim 13,wherein n is 2 when the central metal represents the element belongingto Group
 9. 15. The light-emitting device according to claim 13, whereinn is 1 when the central metal represents the element belonging to Group10.
 16. The light-emitting device according to claim 13, wherein thecentral metal is iridium or platinum.
 17. The light-emitting deviceaccording to claim 13, wherein the layer is a light-emitting layer. 18.The light-emitting device according to claim 13, wherein a molecularweight of the low molecular compound is greater than or equal to 100 andless than or equal to
 150. 19. The light-emitting device according toclaim 13, wherein each of R¹ to R¹⁵ represents hydrogen.